title: Synthesis of syn-4,6-dimethyldodecanal, the male sex pheromone and trail-following pheromone of two species of the termite Zootermopsis.
abstract: Recently, we reported that syn-4,6-dimethyldodecanal is the male sex pheromone and the trail-following pheromone of the Termopsidae Zootermopsis nevadensis and Zootermopsis angusticollis. In this article, we describe the syntheses of the mixture of the four stereoisomers of 4,6-dimethyldodecanal using a synthetic pathway where the key step is a Wittig reaction between methyl 4-methyl-5-oxo-pentanoate and 1-methylheptyl-triphenylphosphonium iodide, and of (±)-syn-4,6-dimethyldodecanal starting from 3,5-dimethyl-2-cyclohexen-1-one. Direct GC-MS comparison of these synthetic samples with the natural pheromone allowed its unambiguous identification.
authors.affiliation: Department of Organic Chemistry, CP 160/06, Faculty of Sciences, University of Brussels, 50 Avenue F. Roosevelt, 1050 Brussels, Belgium.
authors.forename: J
authors.initials: J
authors.lastname: Ghostin
authors.forename: C
authors.initials: C
authors.lastname: Bordereau
authors.forename: J C
authors.initials: JC
authors.lastname: Braekman
mesh_terms: D000818:Animals; D008401:Gas Chromatography-Mass Spectrometry; D017613:Iodine Compounds / Q000737:chemistry; D007536:Isomerism; D020049:Isoptera / Q000737:chemistry*; D008297:Male; D015394:Molecular Structure; D010675:Pheromones / Q000138:chemical synthesis*; D014631:Valerates / Q000737:chemistry
chemical_list: D017613:Iodine Compounds; D010675:Pheromones; D014631:Valerates